Preheat oven to 400 degrees and line Sheetpan with parchment paper or foil.
Toss cubed butternut squash with 2-3 T olive oil and season with salt and pepper. Spread into an even layer on baking sheet and bake for 25-30 minutes, until fork tender and lightly golden.
While squash is roasting, add quinoa, water, and 1/4 tsp salt to a saucepan on the stove. Bring to a boil, then reduce heat, cover and simmer for 15-20 minutes, stirring every 5 minutes or so, until cooked and liquid has been absorbed.
Prepare dressing by adding all ingredients to a bowl or mason jar; whisk or shake to combine. Drizzle a little bit of dressing into warm quinoa and toss to combine.
To assemble, combine roasted butternut squash, cooked quinoa, cranberries, parsley, red onion, and pumpkin seeds in a large bowl. Add more dressing as desired and toss to coat (I like to save some dressing to serve with the leftovers).
If you are serving with arugula, toss in just before serving so it doesn’t wilt.
Store in an airtight container in the fridge for up to 3 days.